(E)-ethyl (4R,5S,6S,7R)-5-azido-4-(benzyloxy)-8-<(tert-butyldimethylsilyl)oxy>-6,7-(isopropylidenedioxy)-2-octenoate

Base Information

Chemical Name:(E)-ethyl (4R,5S,6S,7R)-5-azido-4-(benzyloxy)-8-<(tert-butyldimethylsilyl)oxy>-6,7-(isopropylidenedioxy)-2-octenoate
CAS No.:116375-18-9
Molecular Formula:C₂₆H₄₁N₃O₆Si
Molecular Weight:519.714
Hs Code.:

Synonyms:(E)-ethyl (4R,5S,6S,7R)-5-azido-4-(benzyloxy)-8-<(tert-butyldimethylsilyl)oxy>-6,7-(isopropylidenedioxy)-2-octenoate

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Chemical Property of (E)-ethyl (4R,5S,6S,7R)-5-azido-4-(benzyloxy)-8-<(tert-butyldimethylsilyl)oxy>-6,7-(isopropylidenedioxy)-2-octenoate

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Technology Process of (E)-ethyl (4R,5S,6S,7R)-5-azido-4-(benzyloxy)-8-<(tert-butyldimethylsilyl)oxy>-6,7-(isopropylidenedioxy)-2-octenoate

There total 1 articles about (E)-ethyl (4R,5S,6S,7R)-5-azido-4-(benzyloxy)-8-<(tert-butyldimethylsilyl)oxy>-6,7-(isopropylidenedioxy)-2-octenoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 35.0%

: ethyl (4R,5S,6S,7R)-5-azido-4-(benzyloxy)-8-<(tert-butyldimethylsilyl)oxy>-6,7-dihydroxy-2-octenoate

: 77-76-9
2,2-dimethoxy-propane

: 116375-26-9
(Z)-ethyl (4R,5S,6S,7R)-5-azido-4-(benzyloxy)-8-<(tert-butyldimethylsilyl)oxy>-6,7-(isopropylidenedioxy)-2-octenoate

: 116375-18-9
(E)-ethyl (4R,5S,6S,7R)-5-azido-4-(benzyloxy)-8-<(tert-butyldimethylsilyl)oxy>-6,7-(isopropylidenedioxy)-2-octenoate

Guidance literature:: With camphor-10-sulfonic acid; In acetone; for 2h; Ambient temperature;
DOI:10.1021/jo00257a003

Reference yield:

: 116375-18-9
(E)-ethyl (4R,5S,6S,7R)-5-azido-4-(benzyloxy)-8-<(tert-butyldimethylsilyl)oxy>-6,7-(isopropylidenedioxy)-2-octenoate

: 72741-87-8,96648-51-0,96648-52-1,102208-67-3,107982-28-5,111467-60-8,113299-92-6,116497-15-5,148261-04-5,116497-16-6
(1S,2R,8S,8aS)-octahydro-1,2,8-indolizidinetriol

Guidance literature:: Multi-step reaction with 10 steps

1: H₂ / Raney nickel W-4 / ethanol / 36 h / 760 Torr / Ambient temperature

2: Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

3: pyridine / 3 h / 40 °C

4: K₂CO₃ / dioxane; H₂O / 2 h / 90 °C

5: 64 percent / cyclohexene, 20percent Pd(OH)2/C / ethanol / 26 h / Heating

6: 83 percent / pyridine / 4 h / Ambient temperature

7: 84 percent / dimethylformamide / 0.5 h / 140 °C

8: BH₃-Me₂S / tetrahydrofuran / 2 h / Ambient temperature

9: K₂CO₃ / methanol / 2 h / 65 °C

10: 84 percent / 1 M aq. HCl / 0.5 h / Heating

With pyridine; hydrogenchloride; palladium dihydroxide; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; cyclohexene; Raney nickel W-4; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00257a003